PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    WINTER MAGIC SALE ❄️☃️ Snowy discounts, hot deals!

    First Time Dressing Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    First Cumshot
    Leather Dress
    Dress Bulge
    Short Dress
    Tight Dress
    First Dildo
    First Threesome
    Satin Dress
    Princess Dress
    Good Time
    My First
    First Gangbang
    Dress Room
    Wedding Dress
    First Bareback
    First Facial
    Straight First
    His First
    Summer Dress
    3 Times
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • First dressing video
      01:29
      First dressing video
      Aireon
      3.8K views
    • Fat Sissy Got A New Outfit
      01:11
      Fat Sissy Got A New Outfit
      Chubby Sissy Dani
      3.2K views
    • Joselynne Cd My First Dress Show Ass And Sissy Pussy
      15:51
      Joselynne Cd My First Dress Show Ass And Sissy Pussy
      JoselynneCd
      1.5K views
    • First cross dressing wank
      00:50
      First cross dressing wank
      1.9K views
    • Preview of red dress clip my first unmasked im so nervous he
      05:33
      Preview of red dress clip my first unmasked im so nervous he
      Lizzaali
      2.3K views
    • Joselynne Cd In ExWife Dress My First Dress
      18:07
      Joselynne Cd In ExWife Dress My First Dress
      JoselynneCd
      2.1K views
    • TV RUBBERWHORE MONIQUE - Wearing my whore outfit with facial cunt
      01:55
      TV RUBBERWHORE MONIQUE - Wearing my whore outfit with facial cunt
      GummipuppeMonique
      2.3K views
    • JoseLynne Cd Sexy Mini Dress Show Ass First
      13:06
      JoseLynne Cd Sexy Mini Dress Show Ass First
      JoselynneCd
      1.8K views
    • First half of yellow dress wand play
      09:47
      First half of yellow dress wand play
      Lizzaali
      3.2K views
    • JoseLynne Cd My First Dress Cams
      09:32
      JoseLynne Cd My First Dress Cams
      JoselynneCd
      4K views
    • Sissy Monique - My new outfit & the fcck mask evo
      05:36
      Sissy Monique - My new outfit & the fcck mask evo
      GummipuppeMonique
      934 views
    • JoseLynne Cd My First Dress Cams2
      11:04
      JoseLynne Cd My First Dress Cams2
      JoselynneCd
      2.6K views
    • Joselynne Crossdresser Webcam Using Stockings In First Dress
      31:06
      Joselynne Crossdresser Webcam Using Stockings In First Dress
      JoselynneCd
      2.1K views
    • Teasing dresses up
      04:10
      Teasing dresses up
      brafuckher69
      623 views
    • Crossdresser Samantha Jain First Video Upload
      00:36
      Crossdresser Samantha Jain First Video Upload
      JESSICAJAINB
      1.7K views
    • My First Cheer Uniform (Sporty Version) Outfit Video
      02:10
      My First Cheer Uniform (Sporty Version) Outfit Video
      2.6K views
    • First Time Anal
      08:41
      First Time Anal
      Pure Ts
      78.4K views
    • Trap takes BWC for the first time from daddy
      00:54
      Trap takes BWC for the first time from daddy
      3M views
    • My first time with a trans girl !!
      14:58
      My first time with a trans girl !!
      Lina Mila
      2.1M views
    • HIS FIRST TIME FUCKED BY A LADYBOY AND HE CUM
      01:12
      HIS FIRST TIME FUCKED BY A LADYBOY AND HE CUM
      1M views
    • First Time Glory Hole
      09:03
      First Time Glory Hole
      441.6K views
    • Relevant Short videos

      The first time I decided to follow my heart, I dared to wear a bikini and walk along the beach
      The first time I decided to follow my heart, I dared to wear a bikini and walk along the beach
      Sissylalisa
      2.1K views
      Jaw-dropping moment from "Sexy Ladyboy Striptease Solo Performance Hot Short Dress Big Ass"
      Jaw-dropping moment from "Sexy Ladyboy Striptease Solo Performance Hot Short Dress Big Ass"
      Crossdresserkitty
      241 views
      Powerful moment from "Sexy Ladyboy Striptease Solo Performance Hot Short Dress Big Ass"
      Powerful moment from "Sexy Ladyboy Striptease Solo Performance Hot Short Dress Big Ass"
      Crossdresserkitty
      234 views
      Thrilling moment from "Nightmare Horror Sexy Ladyboy Hot Night Dress Sexy Big Ass Booty Shemale"
      Thrilling moment from "Nightmare Horror Sexy Ladyboy Hot Night Dress Sexy Big Ass Booty Shemale"
      Crossdresserkitty
      205 views
      Captivating moment from "Nightmare Horror Sexy Ladyboy Hot Night Dress Sexy Big Ass Booty Shemale"
      Captivating moment from "Nightmare Horror Sexy Ladyboy Hot Night Dress Sexy Big Ass Booty Shemale"
      Crossdresserkitty
      200 views
      Memorable moment from "Sexy Ladyboy Striptease Solo Performance Hot Short Dress Big Ass"
      Memorable moment from "Sexy Ladyboy Striptease Solo Performance Hot Short Dress Big Ass"
      Crossdresserkitty
      241 views
    • Blonde gurl's first time.
      04:01
      Blonde gurl's first time.
      1.3M views
    • First time with a tranny (shemale) and we enjoy tasty cock
      07:11
      First time with a tranny (shemale) and we enjoy tasty cock
      2.8M views
    • FEMOUT - Cutie Pixie Pond First Time To Show Her Goodies
      03:12
      FEMOUT - Cutie Pixie Pond First Time To Show Her Goodies
      Femout
      20.3K views
    • MY STEPBROTHER WANTS TO TRY FOR THE FIRST TIME WITH A TRANS GIRL
      20:51
      MY STEPBROTHER WANTS TO TRY FOR THE FIRST TIME WITH A TRANS GIRL
      yesid
      1.1M views
    • My first time with a real transsexual...
      08:12
      My first time with a real transsexual...
      She-Male X
      668.5K views
    • FEMOUT XXX - First Time Black Teen petite Tgirl masturbates
      03:11
      FEMOUT XXX - First Time Black Teen petite Tgirl masturbates
      Femout
      660.1K views
    • TRANS ANGELS - Izzy Wilde Meets Her Stepbro Sage Roux For The First Time And In No Time Gets His Cock Out To Suck - TRANS ANGELS
      10:25
      TRANS ANGELS - Izzy Wilde Meets Her Stepbro Sage Roux For The First Time And In No Time Gets His Cock Out To Suck - TRANS ANGELS
      Trans Angels
      750.6K views
    • your first time: she will slowly stretch you and then fuck u
      02:20
      your first time: she will slowly stretch you and then fuck u
      716.9K views
    • Her friends first time taking dick
      03:39
      Her friends first time taking dick
      494.2K views
    • first time taking BWC in ass and i like it. Part 2
      00:39
      first time taking BWC in ass and i like it. Part 2
      1M views
    • M584G02 My son who has returned for the first time in a few years is a transcendental transsexual.
      01:29:57
      M584G02 My son who has returned for the first time in a few years is a transcendental transsexual.
      M MBM3988
      917.4K views
    • Beograd first time with transgirl
      01:59
      Beograd first time with transgirl
      396.7K views
    • Your Very First Time - Trans Femdom GFE with Melissa Masters
      03:40
      Your Very First Time - Trans Femdom GFE with Melissa Masters
      Melissa Masters
      367.4K views
    • Young guy fucked in the ass for the first time by a tranny
      17:25
      Young guy fucked in the ass for the first time by a tranny
      1M views
    • My First Time With a BBC
      08:45
      My First Time With a BBC
      386.3K views
    • First time with my TS stepsister
      01:37
      First time with my TS stepsister
      David Rey
      556.7K views
    • FEMOUT - Introducing The Valentine Fox First Time Lust
      03:12
      FEMOUT - Introducing The Valentine Fox First Time Lust
      Femout
      14.8K views
    • Goth trans girl gets fucked for the first time by a big cock and gets horny by being recorded
      08:05
      Goth trans girl gets fucked for the first time by a big cock and gets horny by being recorded
      Saranji
      71.4K views
    • FEMOUT - Meet and Discover Taylor First Time
      03:12
      FEMOUT - Meet and Discover Taylor First Time
      Femout
      14.3K views
    • A curious woman tries a shemale's cock for the first time
      39:01
      A curious woman tries a shemale's cock for the first time
      Pinko TGirls
      1.6M views
    • boy first time with trans
      10:18
      boy first time with trans
      431.3K views
    • The first time I take a dick in my ass
      02:55
      The first time I take a dick in my ass
      351.5K views
    • My first time with a trans - DVD
      01:38:46
      My first time with a trans - DVD
      Shemale World
      24.3K views
    • First Time Trans Alice Gets Wrecked
      08:12
      First Time Trans Alice Gets Wrecked
      Sampasex Trans
      81.3K views
    • First Time with Milk
      05:27
      First Time with Milk
      ArdaFennec1
      291.7K views
    • Her first time
      01:18
      Her first time
      295.8K views
    Previous page
    Next page
    1
    1. 1
    2. ...
    3. 4
    4. 5
    5. 6
    6. 7
    7. 8
    8. ...
    9. 43
    10. ...
    11. 80
    80

    Searches Related to First Time Dressing

    • Kimberly 13
    • Beautiful Trans Woman
    • Xxx Thailand
    • Slept With Stepmom
    • Real Virgin Porn
    • Transgender Mom
    • Schoolgirl Stepbrother
    • Brother Step Sister Sex
    • Stepbrother Fuck Home Alone Stepsister
    • Mother in Law Crossdresser Whore
    • Stepsisters First Time
    • Thai Ladyboy Fucked
    • Big Misunderstanding
    • Stepdaughter Sneaking Into Dads Room
    • Xxxx Full HD
    • Men Dressed as Woman
    • Sissy Bitch Adult Baby
    • Mature Wife Shared
    • Sexy Trans Fuck Girl
    • Bareback Threesome
    Monetize your content
    Become a creator

    xHamster

    • About us
    • Blog
    • Creator's Blog
    • Advertising
    • xHamster Awards 2025

    Help

    • FAQ
    • Contact us
    • Content Removal
    • Improve xHamster

    Legal

    • Terms of use
    • Privacy policy
    • Cookies policy
    • DMCA/Copyright
    • Parental Controls
    • EU DSA
    • Trust and Safety

    Earn money with us

    • Camgirls Wanted
    • Creator Contest
    • Сontent Creators Program
    © 2026 xHamster - Free porn videos.
    Desktop Version
    18 U.S.C. 2257 Record-Keeping Requirements Compliance Statement
    RTA Restricted To AdultsRTA Restricted To Adults
    xHamster is adults only website!

    The content available on xHamster may contain pornographic materials.

    xHamster is strictly limited to those over 18 or of legal age in your jurisdiction, whichever is greater.

    One of our core goals is to help parents restrict access to xHamster for minors, so we have ensured that xHamster is, and remains, fully compliant with the RTA (Restricted to Adults) code. This means that all access to the site can be blocked by simple parental control tools. It is important that responsible parents and guardians take the necessary steps to prevent minors from accessing unsuitable content online, especially age-restricted content.

    Anyone with a minor in their household or under their supervision should implement basic parental control protections, including computer hardware and device settings, software installation, or ISP filtering services, to block your minors from accessing inappropriate content.

    To enter xHamster you must be 18 or older
    how to protect your minors
    RTA Restricted To AdultsRTA Restricted To Adults